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US 9,844,773 B2Granted
Picolinamide-cinchona organocatalysts and derivatives
AssigneeUniversidade De Evora
InventorsAnthony Burke, Pedro Miguel Cambeiro Barrulas
Life of this patent
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Abstract
The present application describes a novel type of picolinamide-cinchona organocatalyst that allows for the successful transformation of ketimines to chiral amines with very high enantioselectivities and with the highest TOFs reported for any particular organocatalyst to date. These organocatalysts have also been immobilized to a variety of solid supports, including magneto-nanoparticles.
Claims4
An organocatalyst of the formula:
- wherein,
- represents a carbon-carbon single, double or triple bond;
- R represents a hydrogen, a hydroxyl or an alkyl chain;
- R2 represents a hydrogen, an alkyl, a nitro, hydroxyl, amine, cyano or a halogen;
- R1 represents a hydrogen;
- R3 represents an alkyl group;
- the stereochemical configurations at C-8 and C-9, are the only ones that vary;
- X represents, a halide, a triflate, a trifluoroborate, a PF6, a SbF6 or a ClO4.
5 more elements
An organocatalyst wherein a pyridyl ring is fused with a benzene unit thereby providing the following formula IIIa
- wherein,
- represents a carbon-carbon single, double or triple bond;
- R represents a hydrogen, a hydroxyl or an alkyl chain;
- R1 represents a hydrogen;
- R2 represents a hydrogen, an alkyl, a nitro, hydroxyl, amine, cyano or a halogen;
- R3 represents an alkyl group;
- the stereochemical configurations at C-8 and C-9, are the only ones that vary;
- and
- X represents, a halide, a triflate, a trifluoroborate, a PF6, a SbF6 or a ClO4.
6 more elements
An organocatalyst of the formula IV
- wherein
- represents a carbon-carbon single, double or triple bond;
- R represents a hydrogen, a hydroxyl or an alkyl chain;
- R2 represents a hydrogen, a nitro, hydroxyl, amine, cyano or a halogen;
- R1 represents a hydrogen;
- R3 represents an alkyl group;
- the stereochemical configurations at C-8 and C-9, are the only ones that vary;
- X represents, a halide, a triflate, a trifluoroborate, a PF6, a SbF6 or a ClO4;
- L represents a linker;
- and
- said organocatalyst is immobilized with the linker to a support and the linker is attached to said organocatalyst at C-11,
- wherein the linker is an alkyl, a polyoxyalkyl or a polyalkylsulfide chain.
9 more elements
Dependencies are inferred from the claim text.